


Failing Classes

by thelonelywriter



Series: 30 Day OTP NSFW Challenge [28]
Category: Supernatural
Genre: 30 Day OTP Porn Challenge, Alternate Universe - Domestic, Anal Fingering, Anal Sex, Begging, Bottom Castiel, Cock Rings, Dirty Talk, Dom Dean, Light Dom/sub, M/M, Masturbation, Plot What Plot, Porn Without Plot, Punishment, Rough Sex, Shameless Smut, Smut, Spanking, Sub Castiel, Teacher/Student Roleplay, Top Dean, Voyeurism
Language: English
Status: Completed
Published: 2015-08-17
Updated: 2015-08-17
Packaged: 2018-04-15 05:31:58
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,557
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4594698
Author URL: https://archiveofourown.org/users/thelonelywriter/pseuds/thelonelywriter
Summary: <blockquote class="userstuff">
              <p>Dean Winchester and Castiel Novak had been together for years, and they liked to think that they tried a fair amount of stuff in bed. They had vibrators, dildos, handcuffs, and some other toys. They had tried different positions, and they had tried different things overall. But there was one new thing that Castiel was eager to try when he found out about it.</p><p>"Roleplaying?" Dean repeated simply and questioningly whilst he prepared dinner in the kitchen. Castiel smiled and nodded from where he leaned over the island counter.</p>
            </blockquote>





	Failing Classes

**Author's Note:**

> Day Twenty Eight was, 'Roleplaying,' and I'm sorry that I'm late once again, this one had me stumped, okay? Also I'm wicked tired so spare me if there are any mistakes!!

Dean Winchester and Castiel Novak had been together for years, and they liked to think that they tried a fair amount of stuff in bed. They had vibrators, dildos, handcuffs, and some other toys. They had tried different positions, and they had tried different things overall. But there was one new thing that Castiel was eager to try when he found out about it.

"Roleplaying?" Dean repeated simply and questioningly whilst he prepared dinner in the kitchen. Castiel smiled and nodded from where he leaned over the island counter.

"Like the doctor and the patient or the repair man and the client," Castiel began, meandering over to Dean. "But," he said slowly as he wrapped his arms around Dean's waist. "I kind of wanna be your naughty student, and you can be my teacher," he whispered in that certain, slow, gruff voice that always gave Dean goosebumps. 

Dean thought on it for a minute, then decided that, yeah, he was definitely up for that. He grinned, turning to face Castiel, and to give him a sweet kiss. "Sounds good to me."

\---

Two days later, and the two landed in the study, giving one soft kiss before they started. "You ready?" Dean asked quietly, and Castiel nodded vigorously. Dean chuckled, patting his hip. "Alright, go sit down in that chair for me," Dean told Castiel, referencing the chair he had set up across from the desk.

Castiel scurried to the seat, sitting down eagerly as he watched Dean clear his throat with a stern face as he moved behind the desk. And it was then that Castiel knew they had started.

Dean smiled up at Castiel, clasping his hands together. “Mr. Novak, do you know why you’re in my office today?” Dean asked, and Castiel shook his head, letting Dean take the lead. 

Dean pursed his lips and nodded, looking down before making eye contact with Castiel. “Mr. Novak, you’re failing my class,” Dean began. “Is there a reason why you’re failing my class? I know that you’re a very bright student, Mr. Novak,” Dean told Castiel, who thought for a moment. The ball was in his court now, and this was roleplaying after all, he could take him and Dean where he wanted to go, and Dean could do the same.

“Sir, by all means I apologize, it’s just…” Castiel trailed off, leaving Dean hanging as he looked shyly to the floor.

“What is it, Mr. Novak? Has something bad happened recently?” Dean asked, and Castiel had to hide a grin at how good Dean was acting. 

Castiel shook his head, dark hair bouncing as he did. “I’ve been distracted, Sir,” he admitted, and Dean tilted his head just slightly.

“What’s been distracting you, Mr. Novak?” Dean questioned. Castiel peeked up at Dean, his eyes wide and innocent as he answered.

“You, Sir. You’re very distracting to me,” Castiel explained quietly. Dean nodded, a pleased look on his face.

“What about me distracts you?” he inquired plainly. 

“Your voice, y- your body,” Castiel stammered, watching Dean get up from his chair.

“Do you think about me a lot?” Dean questioned as he leaned against the desk. Castiel looked away sheepishly when he answered.

“Yes, Sir, I do,” he responded, and Dean walked a little closer to Castiel.

“In what ways do you think about me, Mr. Novak?” he asked quietly.

“Dirty ways,” Castiel answered, giving Dean a guilty look. Dean clucked his tongue and nodded.

“Take off your jeans, and lean against the desk, you’re getting your punishment now,” Dean told Castiel, who eagerly stripped himself of his shoes, socks, boxers, and jeans to plant his hands on the desk, sticking his ass out. “Don’t move,” Dean instructed as he went back around his desk to grab something from a drawer. “Turn around,” Dean told him, and Castiel groaned internally as he set eyes on the circular rubber ring.

“Don’t pout,” Dean admonished as he slipped the cock ring onto Castiel’s half hard cock. “This is part of your punishment,” Dean told him, letting Castiel turn back around to face the desk.

Castiel only waited one beat before Dean’s hand was coming down on his ass, and the slap of skin on skin echoed throughout the room along with a whimper from Castiel. Another hit landed, and then another, and then Castiel started to really realize why Dean wanted the cock ring on him because he was already getting hard. The mix of pain and the strange pleasure it shot through him created a budding arousal inside of him.

“Tell me why I have to punish you,” Dean ordered gruffly.

“I- I’m failing your class,” Castiel choked out, gaining another rough hit of Dean’s hand.

“What else did you do to earn this pretty little ass of your’s on display, all pink from my hand, huh?” Dean inquired. Castiel squeezed his eyes shut, taking in the sting of every hit.

“I thought dirty thoughts about you,” Castiel murmured.

“Louder,” Dean demanded, and Castiel let out a small groan.

“I thought dirty thoughts about you,” he repeated, this time loud enough to please Dean, whom only laid one last smack down onto Castiel’s ass. 

Dean sighed, sitting back down in the chair he had set up. “Just stand there for a minute, I wanna admire that gorgeous pink ass of yours,” he told Castiel, who couldn’t help but grin, wiggling his ass a little. Dean chuckled behind him.

“You like showing off, don’t you?” Dean asked, gaining a nod over his shoulder from Castiel.

“Good. You’re gonna love what we do next,” Dean told Castiel, and Castiel shivered at the mere tone of his voice. 

Dean let Castiel take a minute or so to simply cool off, and for some of the stinging to go away. But then, he was back up again, walking over to his desk.

Castiel watched as he pulled out a bottle of lube, and placed it on the desk. Castiel gave Dean a confused look, and Dean crossed his arms. “You’re gonna finger yourself for me,” he told Castiel, whose heart sped up. “I want you on the floor, hands and knees. And take off your shirt while you're at it,” Dean ordered, and Castiel complied quickly, throwing his shirt aside and getting down on the floor, making sure that his ass was facing the chair, and that he was far enough away so that Dean could see. 

Dean assessed the position, and nodded with a smile. “Good,” he said, handing Castiel the bottle of lube. “Don’t keep me waiting,” Dean added as he sat down, but he barely needed to say a word because Castiel was already sitting back on his heels, drizzling lube over one finger. He leaned back down, keeping himself up by one hand as the other reached around, finding his rim. He relaxed, sighing into the touch as he slipped one finger in, getting used to the feeling.

“You gonna tell me about all those dirty thoughts, baby?” Dean asked, watching Castiel’s finger slide in and out.

“I- if you want to hear them, Sir,” Castiel said quietly.

“Oh, of course,” Dean responded coolly, leaning back in his chair. Castiel took a deep breath, trying to gather his thoughts. 

“I thought about your body at first. I thought about what you would look like, if you’d have freckles over your chest, if you’d have strong arms…” Castiel trailed off before he began again. “Then I thought about your voice. I thought about all the dirty things you could say to me, that you could whisper in my ear,” Castiel explained.

“What kind of dirty things? Tell me, baby,” Dean murmured, and Castiel bit his lip, pulling his finger out and sitting back to add a little more lube to another one.

“Like how much you’d wanna fuck me. And how you’d fuck me. A- and you’d tell me what a good boy I’ve been so you’d fuck me nice and hard, whispering praises in my ear.” Castiel gulped. “But other times, you’d tell me how naughty I’ve been, what a bad boy I was, so you’d fuck me roughly, pin me down, and I’d let you take me,” Castiel choked out as he tried to keep in a gasp once he got just the right angle, and hit his prostate.

“Keep going,” Dean insisted, feeling his cock growing harder and harder beneath his slacks.

Castiel could feel his own cock hanging hard and heavy beneath him as he spoke, as his fingertips dragged over his prostate.

"I thought about you in my mouth, thought about what your cock would taste like," Castiel groaned. "And I thought about what it would feel like to have you pounding into me," Castiel panted, slipping in a third finger. "What it would be like to have your dick inside of me," he moaned, and Dean quieted his own moan, palming at his hardened cock beneath his slacks.

As Castiel’s fingers thrust in and out he felt a throbbing pleasure inside of him that was just begging to be released. “Sir, please,” he choked out.

“Please, what? Tell me what you want, baby,” Dean said calmly, even though the answer was obvious.

“Fuck me, please,” Castiel begged, and Dean tilted his chin up, looking down at Castiel who was desperately fucking himself back on his own fingers, his hips rolling into the sweet sensations.

“You gonna beg for me, baby?” Dean questioned, his voice growing deeper. Castiel nodded furiously.

“I- I’ll do anything, Sir, just please, want you to fuck me so bad,” Castiel whined.

“Gotta beg better than that baby,” Dean sighed, and Castiel could feel his arm going weak, his cock begging for friction, release, anything.

“Sir, please, I want your cock, want you inside of me. I’ve dreamed about it so many times, wanted it bad for so so long, Sir, please,” he pleaded, praying that Dean would take mercy on him. 

Dean listened to the words, and he could tell that Castiel was sounding utterly fucked out already, so he let up.

“Stand up, and go lean over the desk,” Dean commanded, and Castiel let out a relieved sigh, immediately hastening to bend over the desk like he had before.

Dean, himself, got up from his chair, ridding himself of all his clothes, including his socks and shoes, and went back over to the desk, opening a drawer to grab a condom, and picking up the lube bottle from the floor. “You want me to fuck you hard, baby?” Dean asked as he slid on the condom, pouring on some lube too.

“Yes, Sir, please,” Castiel panted as he felt Dean position himself against his entrance.

“Good,” Dean growled as he draped himself over Castiel, nipping at his ear, and pushing in slowly. Castiel let out a groan at the feeling of being filled, and Dean couldn’t help the soft moan that escaped his lips once he was settled in the tight warmth of Castiel.

The two took a short pause to take a deep breath before Dean grinned, pulling nearly all the way out before slamming roughly back in. Castiel gasped at the force of it, then followed it with a moan. Dean held his hips, slamming them back towards him, setting an experimental pace that quickly grew into a steady, rough one. 

The air grew hot around them as the two began to breathe faster, their hips slamming together as Castiel let out breathy moans and curses beneath Dean. “Does it feel good? Finally having my cock inside of you after so long?” Dean asked through gritted teeth as he ran his hands up Castiel’s sides.

“Yes, fuck, yes,” Castiel breathed out, his own hips grinding back onto Dean’s. He could feel all the pleasure pooled inside of him growing with each and every thrust. 

“You’ve been hungry for it for a long time, haven’t you, baby?” Dean murmured into Castiel’s neck where he was sucking bruises. Castiel simply gave an acknowledging moan in response, biting his lip, and squeezing his eyes shut.

Then, his eyes flew open as Dean found a certain angle that Castiel had been waiting for. “Oh fuck, right there, Sir!” Castiel gasped as the maddening rhythm that had been set was passing over his prostate with every thrust. By now Dean was shoving his hips forward so hard that Castiel was being jolted closer to the desk every time, the desk creaking in protest every once in a while.

Dean ghosted his lips over Castiel's skin, making sure to keep the same angle as he spoke, his thrusts speeding up as he neared his own climax. "Mmm, it feels good being pounded into over the desk, doesn't it, angel? I bet you're glad that you were naughty, glad that you wanted my cock so bad," he growled into Castiel's ear as he desperately fucked into him, chasing his orgasm that he was on the edge of.

"Yes, Sir, yes, fuck, it feels so good," Castiel moaned. It then took only a few thrusts before Dean was coming, his muscles tensing with pleasure as he groaned, flopping his head forward onto Castiel's back, and breathing heavy. 

He took a moment to breathe before he pulled out, then walked over to the waste basket and threw it in before looking over to find a debauched looking Castiel whose hair was wild and eyes were too, his cock hard and aching, cock ring still on. 

Dean grinned, taking in the sight of him. "Think you should come now, baby?" Dean asked, to which Castiel furiously nodded. Dean chuckled a bit before he moved over to Castiel, coaxing him forwards, and slipping off the cock ring, placing it on the desk. He brought Castiel closer, wrapping a hand around Castiel’s cock, earning a gasp from Castiel in return.

Dean leaned his forehead against Castiel's, watching his eyes flutter shut, and his lips part just slightly as he let out a shaky sigh. Dean could tell that Cas was already close just by the way that his eyebrows furrowed, the way his breath hitched with every upstroke of Dean’s hand. 

Castiel grappled for Dean’s shoulders, gripping them tight as he felt himself approaching what he felt was long awaited. “Sir, please,” he panted. “Need more.” Dean kissed him softly, resting his lips against Cas’.

“More it is then, angel,” he said before his hand sped up, before he was making quick, precise movements that had Castiel groaning loudly.

“Sir, gonna-” But he didn’t finish his sentence before he was coming hard with a loud moan, pleasure bursting inside of him, Dean’s name on his lips.

He collapsed into Dean, who smiled, peppering him with kisses before leading him to sit down in the chair. “How was it, huh?” Dean asked softly as he knelt besides the chair. Cas snorted a breath of air.

“Well, you just made me come hard enough so that I could barely see, so I’d say it was pretty fucking good,” he told Dean, who beamed up at him.

“Well it was all thanks to you and your idea to do this,” Dean said, giving Cas a kiss. Castiel smiled into it before Dean pulled away. “You better have more ideas in the future,” Dean proclaimed, and Castiel chuckled.

“Don’t worry, I will.”

**Author's Note:**

> Bing, bang boom, Day Twenty Eight is over and done with! Just warning you, I may be a little late with posting tomorrow's because, like I said, I'm wicked tired, and I'm stumped for the next one too, so just give me like an extra day or two and this challenge will be all done with, even though I know you guys don't want it to be done with :(


End file.
